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The title compound, C9H7BrN2O, was synthesized by the hydrazinolysis of 2-(4-bromo­phen­yl)oxazolo[3,2-a]pyrimidin­ium perchlorate. In the mol­ecule, the oxazole and benzene rings make a dihedral angle of 9.68 (7)°. The crystal packing is stabilized by inter­molecular N—H...N hydrogen bonds and van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038918/cv2126sup1.cif
Contains datablocks global, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038918/cv21262sup2.hkl
Contains datablock 2

CCDC reference: 624198

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.049
  • wR factor = 0.091
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C3 - C31 .. 7.39 su
Alert level C PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C34 - C35 .. 5.42 su
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: WinGX (Farrugia, 1999).

5-(4-bromophenlyl)-1,3-oxazol-2-amine top
Crystal data top
C9H7BrN2ODx = 1.761 Mg m3
Mr = 239.07Melting point: 494(1) K
Orthorhombic, PccnCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ab 2acCell parameters from 25 reflections
a = 39.344 (3) Åθ = 30–33°
b = 7.5684 (8) ŵ = 5.88 mm1
c = 6.0571 (8) ÅT = 293 K
V = 1803.6 (3) Å3Plate, yellow
Z = 80.12 × 0.12 × 0.02 mm
F(000) = 944
Data collection top
Enraf–Nonius CAD-4
diffractometer
1644 reflections with I > 2σ(I)
Radiation source: Fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 75.0°, θmin = 2.3°
ω scansh = 049
Absorption correction: ψ scan
(North et al., 1968)
k = 09
Tmin = 0.539, Tmax = 0.891l = 07
1860 measured reflections1 standard reflections every 60 min
1860 independent reflections intensity decay: 3%
Refinement top
Refinement on F2Secondary atom site location: Difmap
Least-squares matrix: FullHydrogen site location: Geom
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091 w = 1/[σ2(Fo2) + (0.0753P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
1860 reflectionsΔρmax = 0.56 e Å3
127 parametersΔρmin = 0.78 e Å3
4 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: DirectExtinction coefficient: 0.0021 (2)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.54417 (4)1.04294 (14)0.9257 (2)0.0558 (3)
C20.57775 (4)1.0844 (2)0.8783 (2)0.0564 (3)
H20.59141.15630.96590.068*
C30.58809 (4)1.00773 (16)0.6899 (2)0.0506 (3)
C310.61903 (4)1.00097 (15)0.5631 (2)0.0491 (3)
C320.61966 (5)0.9242 (2)0.3553 (2)0.0570 (4)
H320.59970.87830.29650.068*
C330.64947 (4)0.91436 (17)0.2328 (2)0.0545 (3)
H330.64980.86260.09360.065*
C340.67899 (5)0.98533 (19)0.3269 (3)0.0551 (4)
Br340.719801 (6)0.96763 (4)0.15797 (4)0.08280 (16)
C350.67923 (4)1.06160 (19)0.5322 (3)0.0611 (4)
H350.69931.10510.59240.073*
C360.64942 (5)1.0723 (2)0.6463 (2)0.0601 (4)
H360.64921.12840.78300.072*
O40.56008 (3)0.91160 (13)0.61232 (16)0.0542 (3)
C50.53553 (4)0.94253 (15)0.7629 (2)0.0521 (3)
N50.50558 (4)0.8617 (2)0.7307 (3)0.0697 (4)
H5A0.4894 (6)0.871 (4)0.821 (4)0.087 (7)*
H5B0.5026 (5)0.796 (3)0.616 (4)0.081 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0728 (8)0.0441 (6)0.0505 (6)0.0021 (5)0.0025 (6)0.0089 (5)
C20.0716 (9)0.0475 (6)0.0501 (7)0.0074 (6)0.0029 (6)0.0031 (5)
C30.0740 (8)0.0275 (5)0.0503 (7)0.0002 (5)0.0046 (6)0.0012 (5)
C310.0668 (7)0.0299 (5)0.0507 (7)0.0001 (5)0.0027 (6)0.0015 (5)
C320.0785 (10)0.0458 (6)0.0467 (7)0.0018 (7)0.0022 (6)0.0068 (5)
C330.0813 (9)0.0332 (5)0.0491 (7)0.0060 (6)0.0016 (7)0.0073 (5)
C340.0663 (9)0.0405 (6)0.0583 (9)0.0032 (6)0.0027 (6)0.0035 (6)
Br340.0753 (2)0.0885 (2)0.0846 (2)0.00489 (9)0.01464 (9)0.00479 (10)
C350.0676 (9)0.0484 (7)0.0673 (10)0.0121 (6)0.0023 (7)0.0006 (6)
C360.0736 (8)0.0627 (8)0.0440 (7)0.0025 (7)0.0039 (6)0.0041 (6)
O40.0647 (6)0.0478 (5)0.0501 (5)0.0024 (4)0.0002 (4)0.0080 (4)
C50.0738 (8)0.0308 (6)0.0516 (7)0.0011 (5)0.0014 (7)0.0021 (5)
N50.0746 (8)0.0702 (9)0.0644 (8)0.0149 (7)0.0122 (7)0.0243 (7)
Geometric parameters (Å, º) top
N1—C51.2905 (19)C33—H330.9300
N1—C21.388 (2)C34—C351.371 (2)
C2—C31.343 (2)C34—Br341.9089 (19)
C2—H20.9300C35—C361.364 (3)
C3—O41.4015 (18)C35—H350.9300
C3—C311.440 (2)C36—H360.9300
C31—C321.387 (2)O4—C51.3493 (19)
C31—C361.406 (2)C5—N51.342 (2)
C32—C331.390 (2)N5—H5A0.84 (3)
C32—H320.9300N5—H5B0.86 (2)
C33—C341.401 (2)
C5—N1—C2103.06 (13)C35—C34—C33122.44 (16)
C3—C2—N1111.47 (14)C35—C34—Br34120.66 (13)
C3—C2—H2124.3C33—C34—Br34116.90 (12)
N1—C2—H2124.3C36—C35—C34118.60 (16)
C2—C3—O4105.74 (15)C36—C35—H35120.7
C2—C3—C31136.40 (15)C34—C35—H35120.7
O4—C3—C31117.85 (12)C35—C36—C31121.79 (15)
C32—C31—C36118.14 (15)C35—C36—H36119.1
C32—C31—C3120.94 (14)C31—C36—H36119.1
C36—C31—C3120.92 (13)C5—O4—C3104.25 (11)
C31—C32—C33121.46 (16)N1—C5—N5127.66 (15)
C31—C32—H32119.3N1—C5—O4115.48 (14)
C33—C32—H32119.3N5—C5—O4116.82 (12)
C32—C33—C34117.52 (14)C5—N5—H5A122.0 (17)
C32—C33—H33121.2C5—N5—H5B120.1 (14)
C34—C33—H33121.2H5A—N5—H5B118 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···N1i0.84 (3)2.12 (3)2.947 (2)165 (3)
Symmetry code: (i) x+1, y+2, z+2.
 

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